Diterpenes from Alomia myriadenia (Asteraceae) with cytotoxic and trypanocidal activity

Scio, Elita; Ribeiro, Antônia; Alves, Tânia Maria de Almeida; Romanha, Álvaro J.; Filho, José Dias de Souza; Cordell, Geoffrey A.; Zani, Carlos L.

doi:10.1016/s0031-9422(03)00529-6

Cited by 45 publications

(36 citation statements)

References 17 publications

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“…Da avaliação destes três diterpenos, o último foi o que se mostrou mais ativo, quando testado in vitro contra formas tripomastigotas de T. cruzi em sangue infectado de murinos, causando a lise de 100% dos parasitas na concentração de 250 µg/mL (Scio et al, 2003) (Figura 8).…”

Section: Terpenosunclassified

Substâncias da natureza com atividade anti-Trypanosoma cruzi

Saúde-Guimarães¹,

Faria²

2007

Rev. bras. farmacogn.

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RESUMO:A doença de Chagas, uma zoonose causada por Trypanosoma cruzi, afeta em todo o mundo cerca de 16 a 18 milhões de pessoas. Sua transmissão ocorre através das fezes de triatomíneos, insetos hematófagos conhecidos como barbeiro. Atualmente, a principal forma de transmissão da doença de Chagas em áreas urbanas é por meio de transfusão de sangue contaminado. A violeta de genciana é o único agente que pode ser empregado na quimioprofi laxia de sangue destinado à transfusão. No entanto, existem algumas restrições ao seu uso. A quimioterapia disponível para a doença de Chagas não é efi caz uma vez que as drogas disponíveis nifurtimox e benznidazol são ativas apenas na fase aguda da doença e apresentam sérios efeitos colaterais. Várias substâncias isoladas de plantas foram avaliadas como agentes anti-T. cruzi, objetivando encontrar drogas com menos efeitos colaterais e maior efi cácia para a quimioprofi laxia e quimioterapia da doença de Chagas. Nesta revisão são apresentadas as substâncias de origem natural com atividade anti-T. cruzi.

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Section: Terpenosunclassified

Substâncias da natureza com atividade anti-Trypanosoma cruzi

Saúde-Guimarães¹,

Faria²

2007

Rev. bras. farmacogn.

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“…In this study four plants known for their biological activities were selected to endophytic fungi recovered. Palicourea tetraphylla has been used in traditional Brazilian medicine to treat tumours of joints and limbs, and indurations of the prostate (11); Piptadenia adiantoides, popularly known as "Calombi-branco" is used as food and for handcrafting (4); Ageratum myriadenia produce metabolites with cytotoxic and trypanocidal activities (27); and Trixis vauthieri has the ability to produce trixol, a trypanocidal compound active against the protozoan tropical parasite T.…”

Section: Introductionmentioning

confidence: 99%

Leishmanicidal, trypanocidal, and cytotoxic activities of endophytic fungi associated with bioactive plants in Brazil

Rosa¹,

Gonçalves²,

Caligiorne³

et al. 2010

Braz. J. Microbiol.

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One hundred and twenty-one isolates of endophytic fungi were recovered from leaves of the bioactive Brazilian plant species Ageratum myriadenia, Palicourea tetraphylla, Piptadenia adiantoides, and Trixis vauthieri. All fungal isolates were cultivated in liquid media and crude extracts were obtained with ethyl acetate. The crude extracts were tested in bioassay panels using Leishmania amazonensis, Trypanosoma cruzi, the enzyme trypanothione reductase (TryR) from Trypanosoma cruzi, and three human cancer cell lines. Thirty-three extracts (27.2%) exhibited at least one biological activity. Seventeen extracts (14%) were cytotoxic against one or more human cancer cell line with the IC 50 values ranged of >0.2 to 25 µg/mL. Twenty-four extracts (19.8%) inhibited the activity of TryR, and three showed ability to inhibit the growth of T. cruzi above 60% and their IC 50 values ranged among 1 to 10 µg/mL. Eleven extracts (9%) were able to inhibit the growth of L. amazonensis and showed with IC 50 values ranged among 4.6 to 24.4 µg/mL. The endophytic fungi were identified as belonging to the genera Alternaria, Arthrinium, Cochliobolus, Colletotrichum, Penicillium, Fusarium, and Gibberella. An interesting result was obtained for the bioactive isolates UFMGCB 508, 537, 899 and 903, which were related to fungi associated with medicinal plants native to Asia, Australia, Africa, and Polynesia. These results indicate that bioactive plants living in Brazilian ecosystems are a potential host of endophytic fungi able to produce bioactive prototype molecules for drug development against neglected tropical diseases.

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“…Unfortunately, NOESY correlations between H-16 (d H 6.06) and both H-11 (d H 1.94, 2.11) were observed with the same intensity which prevents the determination of the stereochemistry of the hydroxyl function at C-16. However, while some authors observed both epimers at H-16 of related compounds, 17,18) its single signal in the 1 H-and 13 C-NMR spectra suggests that only one epimer was isolated.…”

Section: Resultsmentioning

confidence: 93%

A New Labdane Diterpene from the Flowers of Solidago canadensis

et al. 2008

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Solidago canadensis L. is an Asteraceae widely distributed across North America, occurring in almost every state of the U.S.A. and throughout Canada. Numerous interesting secondary metabolites such as: flavonoids, phenolic acids and glucosides, polysaccharides, diterpenes, triterpenoid saponosides, tannins and essential oils 1) were reported for the genus Solidago. Previous phytochemical studies of S. canadensis have led to the isolation of flavonoids, 2,3) phenolic acids, 4) sesquiterpenes, 5) diterpenes 6,7) and saponins.7) The flowers of S. canadensis were used in traditional Amerindian medicine as an analgesic, 8) burns and ulcers treatment, 9) febrifuge, 10) gastrointestinal 11,12) and liver 11) aids. In spite of the widespread use of S. canadensis, few investigations were carried out on its bioactive secondary metabolites.Fractionation of the flower extracts of Solidago canadensis resulted in the isolation of a new diterpene, 9a,16x-dihydroxy-6-oxo-7,13-labdadien-15,16-olide (solicanolide, 1) and six known compounds identified as quercetin (2), 3-O-caffeoylquinic acid (neochlorogenic acid) (3), 5-O-caffeoylquinic acid (chlorogenic acid) (4), 4,5-di-O-caffeoylquinic acid (5), 3,5-di-O-caffeoylquinic acid (6) and 3,4-di-O-caffeoylquinic acid (7). To our knowledge, compound 7 was isolated for the first time in S. canadensis. This work describes the isolation of compounds 1-7 and the structure elucidation of a new compound identified as compound 1. The cytotoxicity of solicanolide (1) was also investigated in this paper. ExperimentalGeneral Experimental Procedures NMR spectra were recorded in methanol-d 4 on a Bruker Avance 400 spectrometer (5 mm QNP with Z-gradient probe) operating at 400.13 MHz ( 1 H) or 100.61 MHz ( 13 C). Chemical shifts were referenced relative to the corresponding residual solvent signals (d H/C 3.31/49.0 ppm, respectively). The accurate mass determination was carried out with an Applied Biosystems QSTAR XL Hybrid LC/MS/MS system. Optical rotation was obtained on a Jasco DIP-360 digital polarimeter. Analytical HPLC-DAD-MS analysis were performed on an Agilent 1100 series HPLC-DAD-MS system. A Zorbax ODS C18 column (5 mm, 150ϫ4.6 mm) maintained at 25°C was utilised. The flow rate was 1 ml/min. Agilent G1315B diode array detector was used for UV detection. The UV spectra were recorded from 190 to 400 nm. An Agilent mass selective detector (VL model) equipped with an atmospheric chemical ionisation source (APCI) was employed for MS detection. All mass spectra were acquired in the negative ion mode. The full scan mass spectrum was recorded over the range of m/z 100-1000. Temperature of the drying gas (N 2 ) was 350°C with a gas flow rate of 10 l/min and a nebulizing pressure of 40 psi. The ionisation voltage was 4000 V and the corona current was 15 mA. All HPLC separations were performed on a preparative Agilent 1100 series (Agilent Technologies Canada Inc.) with a ZORBAX ODS column C18 (2.1ϫ25 cm; 7 mm) at a flow rate of 16 ml/min. Compounds were detected by UV absorption at 254 nm. For all...

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Diterpenes from Alomia myriadenia (Asteraceae) with cytotoxic and trypanocidal activity

Cited by 45 publications

References 17 publications

Substâncias da natureza com atividade anti-Trypanosoma cruzi

Substâncias da natureza com atividade anti-Trypanosoma cruzi

Leishmanicidal, trypanocidal, and cytotoxic activities of endophytic fungi associated with bioactive plants in Brazil

A New Labdane Diterpene from the Flowers of Solidago canadensis

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